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. Author manuscript; available in PMC: 2012 Aug 17.
Published in final edited form as: J Am Chem Soc. 2011 Jul 22;133(32):12458–12461. doi: 10.1021/ja205674x

Table 2.

Asymmetric isomerization of 8a to 9a by a cinchona alkaloid bearing a 6' hydrogen bonding donora

graphic file with name nihms312905t2.jpg

entry catalyst T(°C) Time conv.(%)b ee(%)b
1 1a rt 10min 20 67
2 1b rt 10min 16 60
3 1c rt 10min 12 74
4 3a rt 10min 5 60
5 3b rt 10min 5 63
6 6 rt 10min 55 64
7 Q-7 rt 10min 33 84
8 QD-7 rt 10min 57 −86
9 QD-7 −20 24h 36 −92
10 QD-7 −20 72h 80 −90
a

Unless noted, reactions were run with 0.05 mmol of 8a in 0.05 mL of CH2Cl2 with 10 mol% catalyst. See supporting information for details.

b

Determined by HPLC analysis.